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WO2003043433A1 - Produits alimentaires prepares contenant des phytosterols non esterifies recristallises par triglycerides - Google Patents

Produits alimentaires prepares contenant des phytosterols non esterifies recristallises par triglycerides Download PDF

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Publication number
WO2003043433A1
WO2003043433A1 PCT/US2002/036809 US0236809W WO03043433A1 WO 2003043433 A1 WO2003043433 A1 WO 2003043433A1 US 0236809 W US0236809 W US 0236809W WO 03043433 A1 WO03043433 A1 WO 03043433A1
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WO
WIPO (PCT)
Prior art keywords
phytosterols
fat
oil
esterified
food product
Prior art date
Application number
PCT/US2002/036809
Other languages
English (en)
Inventor
Daniel Perlman
Kenneth Hayes
Andrzej Pronczuk
Original Assignee
Brandeis University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Brandeis University filed Critical Brandeis University
Priority to AT02789698T priority Critical patent/ATE446013T1/de
Priority to DE60234120T priority patent/DE60234120D1/de
Priority to AU2002352747A priority patent/AU2002352747A1/en
Priority to EP02789698A priority patent/EP1453386B9/fr
Publication of WO2003043433A1 publication Critical patent/WO2003043433A1/fr
Priority to US10/677,634 priority patent/US7144595B2/en
Priority to US11/475,575 priority patent/US7709038B2/en
Priority to US12/772,084 priority patent/US8187657B2/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/10—Products from fruits or vegetables; Preparation or treatment thereof of tuberous or like starch containing root crops
    • A23L19/12—Products from fruits or vegetables; Preparation or treatment thereof of tuberous or like starch containing root crops of potatoes
    • A23L19/18—Roasted or fried products, e.g. snacks or chips
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L25/00—Food consisting mainly of nutmeat or seeds; Preparation or treatment thereof
    • A23L25/10—Peanut butter
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen

Definitions

  • the present invention relates to prepared foods, such as fried snack foods, fortified with non-esterified phytosterols delivered in fats or oils that are essentially free of emulsifiers and the like, and to the utility of such phytosterols for stabilizing heated fats and, oils against oxidation, as well as to the surprising bioavailability of triglyceride-recrystallized phytosterols in such foods, for decreasing plasma cholesterol levels in mammals.
  • phytosterols i. e. , either plant sterols, stanols, or combinations thereof [including beta- sitosterol, beta-sitostanol, campesterol, campestanol, stigmasterol, stigmastanol, brassicasterol, brassicastanol, clionasterol and clionastanol (collectively termed phytosterol or phytosterols)] for lowering plasma cholesterol, the phytosterol should be dissolved in an edible oil or other solvent so that it can enter micelles in the small intestine to inhibit the absorption of cholesterol.
  • phytosterols such as alpha and beta sitosterol, stigmosterol, campesterol, and the corresponding saturated (chemically reduced or hydrogenated) "stanol" species, are insoluble in water, and only slightly soluble in edible oils. Accordingly, to promote the solubilization of phytosterols, and their efficacy in lowering plasma cholesterol, U.S. Pat. No. 6,025,348 by Goto et al.
  • a polyhydric alcohol/fatty acid ester including glycerol fatty acid esters containing at least two esterified and at least one unesterified hydroxyl group such as diacylglycerols or diglycerides
  • a polyhydric alcohol/fatty acid ester including glycerol fatty acid esters containing at least two esterified and at least one unesterified hydroxyl group such as diacylglycerols or diglycerides
  • U.S. Pat. No. 6,139,897 by Goto et al. describes an oil or fat composition containing 80% or more diacylglycerol and up to 20% phytosterol.
  • the high proportion of diacylglycerol assures solubility or dispersal of the phytosterol to provide a cholesterol-lowering fat substitute.
  • U.S. Pat. No. 5998,396 by Nakano et al. describes an edible oil containing a phytosterol, vitamin E, and an emulsifier rendering the phytosterol soluble in both the vitamin E and the edible oil.
  • U.S. Pat. No. 5,419,925 by Seiden et al. describes a reduced calorie fat composition based upon a substantially non-digestible polyol fatty acid polyester plus reduced calorie medium chain triglycerides and other reduced calorie fats or noncaloric fat replacements including plant sterol esters that are soluble in such fat compositions. Free fatty acids, vitamin E and tocotrienol have each been utilized by other inventors to promote the solubilization of phytosterols in fats and oils, with the expectation that the cholesterol lowering properties of various phytosterols would be improved. [0009] U.S. Pat. No.
  • a cholesterol- lowering food additive composition with plant stanols, including: (i) an edible carrier such as an oil, monoglyceride, diglyceride, triglyceride, tocopherol, alcohol or polyol, (ii) an antioxidant and (iii) a dispersant or detergent-like material such as lecithin, or other phospholipids, sodium lauryl sulfate, a fatty acid, salts of fatty acids, or a fatty acid ester.
  • an edible carrier such as an oil, monoglyceride, diglyceride, triglyceride, tocopherol, alcohol or polyol
  • an antioxidant and
  • a dispersant or detergent-like material such as lecithin, or other phospholipids, sodium lauryl sulfate, a fatty acid, salts of fatty acids, or a fatty acid ester.
  • Straub cites research showing that 1.5 grams per day of a stanol mixture derived from soybean sterols lowered blood cholesterol by 15% after 4 weeks of therapy, and believes that these stanols are preferred to sterols based upon less stanol absorption from the G.I. tract and better heat stability in air than sterols.
  • U.S. Pat. No. 5,932,562 by Ostlund, Jr. describes an aqueous micellar mixture of plant sterol and lecithin (in a 1 : 1 to 1 : 10 mole ratio) which has been dried to a water soluble powder and which is useful as a food additive for reducing cholesterol absorption.
  • U.S. Pat. No. 4,195,084 by Ong describes a taste-stabilized pharmaceutical suspension of sitosterols to reduce hypercholesterolemia, in which the suspension includes the plant sterol, a chelator such as calcium disodium EDTA, a surfactant and other ingredients to assure suspension and dispersal of the phytosterol.
  • a chelator such as calcium disodium EDTA
  • surfactant such as calcium disodium EDTA
  • other ingredients to assure suspension and dispersal of the phytosterol.
  • U.S. Pat. No. 3,881 ,005 by Thakkar et al. describes a pharmaceutical dispersible powder for oral administration in which sitosterols are combined with any one of a variety of excipients, and any one of a variety of pharmaceutically acceptable surfactants.
  • U.S. Pat. No. 6,267,963 by Akashe et al. describes a plant sterol/emulsifier complex that has a lower melting temperature than the plant sterol alone.
  • the complex e.g., a co-crystallized monoglyceride and plant sterol mixture, is said to facilitate incorporation of the sterol into food products without adversely affecting the texture of the food products.
  • U.S. Pat. Nos. 6,031,118 and 6,106,886 by van Amerongen et al. describe similar stanol fatty acid esters but provide different and reportedly improved chemical methods for their preparation.
  • Plant sterols(from soybean oil) have also been interesterified with fatty acid esters to produce the margarine marketed under the tradename Take Control®.
  • Clinical studies suggest that with mildly hypercholesterolemic individuals, dietary intake of between 1.5 and 3 grams per day of the free phytosterol (provided in a fatty acid esterified form) is required to decrease plasma cholesterol approximately 15%.
  • microparticulate phytosterols described in the prior art involves increased cost and inconvenience, e.g., the use of grinding, and can result in a mixed emulsified product that is more susceptible to oxidation and rancidity, particularly when an aqueous fat-phytosterol emulsion is involved.
  • methods of phytosterol preparation and delivery have included grinding, formation of fat and water mixed phytosterol emulsions, chemical modification of phytosterols, e.g., esterification, and mixing of phytosterols with substantial amounts of specialized solubilizing and dispersing agents.
  • the present invention concerns the use of non-esterified phytosterols in fortifying fat-containing prepared foods.
  • Non-esterified phytosterols were found to have the unexpected property of decreasing the oxidation of fats used in prepared foods, particularly when the fats are heated and become particularly susceptible to oxidation. It is believed that soluble phytosterols e.g., the heat-solubilized non- esterified phytosterols described herein, are also able to protect polyunsaturated fatty acid moieties in fats by quenching, i.e., scavenging, oxidative free radicals and/or peroxides and hydroperoxides that are formed during fat oxidation, and that are particularly problematic in heated fats.
  • phytosterols can actually protect fats against oxidation during cooking and storage.
  • These two different and compatible functionalities each support the novel introduction of phytosterols into fat-based compositions or fat-containing prepared foods, e.g., into frying and baking shortenings that are absorbed (e.g., into potato chips) or otherwise incorporated into such prepared foods.
  • TRPs triglyceride-recrystallized non-esterified phytosterols
  • Such more costly phytosterols include microparticulate powders (ultrafine micron-sized phytosterol powders), chemically modified fat-soluble phytosterols, e.g., fatty acid-esterified phytosterols, emulsified phytosterols, and the more perishable water-oil microparticulate suspensions of phytosterols.
  • microparticulate powders ultrafluine micron-sized phytosterol powders
  • chemically modified fat-soluble phytosterols e.g., fatty acid-esterified phytosterols, emulsified phytosterols
  • the more perishable water-oil microparticulate suspensions of phytosterols Underlying this new method for utilizing phytosterols is the discovery that although a chemically unmodified phytosterol (such as beta-sitosterol) is insoluble in water and poorly soluble in fat, it need not be converted to a microparticulate powder to be effective at reducing plasma cholesterol levels in vivo.
  • this invention provides a prepared food product for ingestion by mammals, e.g., by humans.
  • the food product includes an oxidation- resistant fat-based composition substantially free of exogenous solubilizing and dispersing agents for phytosterols.
  • This fat-based composition includes between 75% and 98%o by weight of at least one triglyceride-based edible oil or fat, and between 2% and 25% by weight of non-esterified tryglyceride-recrystallized phytosterols (TRPs).
  • TRPs non-esterified tryglyceride-recrystallized phytosterols
  • At room temperature a limited amount of phytosterol will solubilize, typically such that a fat will include approximately 1.5% by weight of the phytosterols in solution, with any remaining phytosterols remaining insoluble.
  • the fat composition will contain approximately 1.5% solubilized phytosterol and between 0.5% and 23.5% by weight of the phytosterols will remain insoluble at that temperature.
  • the fat- based composition has been partially oxidized by an interval of exposure to air during the manufacture and storage of the prepared food product, and contains a reduced amount of oxidative by-products compared to a similar fat-based composition lacking these non-esterified phytosterols.
  • Storage stability of the food product may also be referred to as the shelf-life of the product at ambient temperatures.
  • the shelf life for such products may range from approximately one week to a year or more.
  • This fat-based composition has been shown to be cholesterol-reducing as measured in the plasma of mammals, and the TRPs when ingested, are essentially as effective, i.e., as bioavailable, as fat-soluble esterified phytosterols in lowering plasma cholesterol levels.
  • the shelf-life of a prepared food product containing TRPs is increased at least 5%, 10%, 20%, 30%, 50%, 100%, or even more compared to an otherwise equivalent food product not containing the TRPs.
  • the fat composition includes phytosterols at a level of 2-5%, ' 5-10%, 10-15%, 15-20%, or 20-25%. In some cases even higher levels may be added.
  • a prepared food product for ingestion by mammals is provided as above except that the fat-based or fat-containing composition has been partially oxidized by an interval of heating, e.g., frying, baking, cooking and the like, in air, and contains a reduced amount of oxidative by-products compared to a similar fat- based composition lacking said non-esterified phytosterols.
  • An upper limit for the interval of heating in air has not been established.
  • any duration of heating of a conventional fat one that is free of phytosterols
  • results in an acceptable not excessive accumulation of oxidative by-products, (such as free fatty acids and conjugated dienes)
  • oxidative by-fortified fat for example, fats and vegetable oils may be exposed to temperatures of approximately
  • a prepared food product as described above may be fried, baked or otherwise heated at least for a time period and to a temperature at least sufficient to dissolve a desired amount (preferably all) of the non-esterified phytosterols added to the fat portion of the fat composition.
  • the fat composition is substantially free of exogenous phytosterol- solubilizing and dispersing agents.
  • Phytosterol enrichment of the fat composition decreases the amount of polar and other oxidative by-products accumulated in the fat and in the prepared food during heating and exposure to air. At least a portion of the non-esterified phytosterols in the fat composition are converted by heating, fully dissolving and subsequent cooling, to triglyceride-recrystallized phytosterols, i.e. TRPs, in which the TRPs contained in the fat composition and in the prepared food product are bioavailable when ingested, to reduce mammalian plasma cholesterol levels.
  • TRPs triglyceride-recrystallized phytosterols
  • the amount of the edible fat composition in the prepared food product is between 10% and 75% by weight of the food product, e.g., 10- 20%, 20-30%, 30-40%, 40-50%, 50-60%, or 60-75%. In other embodiments, the amount of the edible fat composition in the prepared food is lower or higher, e.g., 1- 5%, 2-5%, 3-5%, or 4-5%.
  • the TRPs are formed by heating at least the fat- based composition (or heating the prepared food product as it contains the fat-based composition) to a temperature of greater than 60°C, and fully dissolving the non- esterified phytosterols in the fat composition, and subsequently cooling this composition to room temperature to allow the TRPs to crystallize and be formed.
  • a prepared food product for ingestion by mammals includes a plasma cholesterol-reducing oil or fat composition with improved resistance to oxidation.
  • the oil or fat composition is substantially free of exogenous solubilizing and dispersing agents for phytosterols, and includes between 75% and 95% by weight of at least one triglyceride-based edible oil or fat, and at least 5% by weight of non-esterified triglyceride-recrystallized phytosterols.
  • the phytosterols are soluble in the oil or fat composition at room temperature to a level of approximately 1.5% by weight, so that at least 3% by weight of phytosterols are insoluble at room temperature and have been converted by heating, fully dissolving, and cooling to form triglyceride-recrystallized phytosterols, i.e., TRPs.
  • TRPs triglyceride-recrystallized phytosterols
  • the oil or fat composition includes at least 8%, 10%, 12%, 15%, 17%), or 20% by weight of non-esterified phytosterols or is in a range defined by taking any two of those values as endpoints of the range.
  • typically the phytosterols are soluble in the fat or oil at room temperature to a level of approximately 1.5% by weight, and the remainder (e.g., at least 6.5%, 8.5%,
  • TRPs 10.5%), 12.5%, 15.5%), or 17.5% respectively
  • a TRP Tryglyceride-recrystallized by heating to dissolve the phytosterols and cooling.
  • TRPs when ingested, are essentially as effective as fat-soluble esterified phytosterols in lowering plasma cholesterol levels in mammals.
  • the TRPs described above are formed by heating at least the above referenced oil or fat composition (or a prepared food product containing the oil or fat composition, or the oil or fat and the phytosterols as ingredients of the prepared food) to a temperature of greater than 60°C, fully dissolving the non-esterified phytosterols in the composition, and subsequently cooling the composition to room temperature to cause the TRPs to be formed.
  • prepared food products are selected from the group consisting of margarine, frying and baking shortenings, mayonnaise, salad dressing, filled dairy products, nut, seed and kernel butters and chocolate (containing cocoa butter).
  • the phytosterols are dissolved by heating them in the fat portion of these prepared foods, t.e., heating without any aqueous components present.
  • the prepared food product is a pastry or cake.
  • the prepared food product is fried, baked, or otherwise heat-processed with the oil or fat composition, and/or where the oil or fat composition and phytosterols are added as ingredients in the preparation of the prepared food, wherein such heating allows a portion of non-esterified phytosterols that is insoluble in the oil or fat composition at room temperature to be solubilized and thereby enter and be incorporated into the food product, whereupon during cooling, TRPs are formed in the food product.
  • the prepared food product is selected from the group consisting of potato chips, French fries, corn chips, tortilla chips, popcorn, and crackers.
  • the food product is cooked, baked, or otherwise heat-processed with the above-described oil or fat composition, allowing a portion of non-esterified phytosterols that is insoluble in the composition at room temperature to be solubilized.
  • a partial or complete solidification of the oil or fat composition can occur. This solidification decreases the oiliness, particularly the surface oiliness, perceived by hand contact with the food product compared to the same food product prepared without non-esterified phytosterols (due to the formation of TRPs in the fat or oil).
  • Solidification or "hardening'Of oil” can also reduce or prevent oil separation in certain prepared foods, and is particularly useful in such foods as peanut butter, soybean butter, sesame seed butter and other seed, bean and nut kernel butters.
  • Hardening of an edible oil may be compared to that resulting from partial hydrogenation of vegetable oils. Both modifications tend to solidify a vegetable oil by increasing the oil's melting temperature.
  • addition of phytosterols to ones diet advantageously decreases the level of plasma LDL cholesterol, while addition of partially hydrogenated oils disadvantageously increases the LDL level.
  • the food product, and more particularly the oil or fat composition within the food product, when heated in air, is more resistant to oxidation and formation of chemically polar degradation products than the same product lacking the non-esterified phytosterols, e.g., as described in Example 3 below.
  • the food product incorporating the oil or fat composition has a reduced calorie content compared to a similar food product prepared without non-esterified phytosterols, owing to the presence of the non-esterified phytosterols that are calorie-free, and substitute for a portion of triglyceride-based oil or fat normally absorbed or otherwise incorporated into the food product. This statement is explained and supported by Example 4 below.
  • the non-esterified phytosterols are selected from the group consisting of tall oil-derived phytosterols (such as those obtained from the manufacture of wood pulp from pine trees) and vegetable oil-derived phytosterols (such as those derived from soybean oil).
  • the invention provides an oxidation-resistant frying or baking shortening that includes: (a) from 75%) to 98% by weight of at least one edible triglyceride-based fat or oil; and (b) from 2.0% to 25% by weight TRPs (produced from at least one non-esterified phytosterol compound being solubilized by heating, and allowed to recrystallize in the fat or oil upon cooling).
  • TRPs produced from at least one non-esterified phytosterol compound being solubilized by heating, and allowed to recrystallize in the fat or oil upon cooling.
  • typically from 0.5% to 23.5% by weight of phytosterols are recrystallized in the solid phase, and approximately 1.5% by weight of non-esterified phytosterol remains solubilized in the fat at room temperature.
  • the shortening is substantially free of exogenous solubilizing and dispersing agents for phytosterols, and the rate of formation of polar oxidation products upon heating the shortening to between 160°C and 190°C is reduced, compared to the same shortening lacking the at least one non-esterified phytosterol compound.
  • the formation of polar oxidation products was determined by measurement of the dielectric constant of the shortening after two hours of heating as described elsewhere herein (see Example 3, second experiment).
  • the term "reduced,” referring to the rate of formation of polar oxidation products, indicates that the increase in dielectric constant of the shortening is reduced at least 5%, and preferably 7, 8, or 10% or more for the phytosterol-supplemented shortening, compared to the non-supplemented shortening.
  • the oxidation-resistant frying or baking shortening includes at least one edible triglyceride-based fat or oil selected from the group consisting of natural vegetable oils or fats, natural animal fats and oils, structurally rearranged or modified vegetable and/or animal fats, and combinations thereof.
  • the oxidation-resistant frying or baking shortening includes at least one non-esterified phytosterol compound selected from the group consisting of vegetable oil-derived phytosterols, tall oil-derived phytosterols, and combinations thereof.
  • the oxidation-resistant frying or baking shortening includes at least one non-esterified phytosterol selected from the group consisting of beta-sitosterol, beta-sitostanol, campesterol, campestanol, stigmasterol, stigmastanol, brassicasterol, brassicastanol, clionasterol and clionastanol, and combinations thereof.
  • the invention features a method for reducing plasma cholesterol levels in mammals.
  • the method includes providing a heat-processed prepared food containing an edible fat-based composition that includes between 75% and 98% by weight of at least one triglyceride-based edible fat, and between 2% and 25% by weight of non-esterified triglyceride-recrystallized phytosterols, for ingestion by the mammal(s).
  • the phytosterol is soluble to a level of approximately 1.5% by weight, such that the insoluble phytosterols in the fat-based composition at room temperature constitute between 0.5% and 23.5%.
  • the fat-based composition is substantially free of exogenous phytosterol-solubilizing and dispersing agents.
  • the insoluble phytosterols have been heat-solubilized and subsequently cooled to form triglyceride-recrystallized phytosterols i.e., TRPs.
  • TRPs triglyceride-recrystallized phytosterols
  • the TRPs when ingested are essentially as effective as fat-soluble esterified phytosterols in reducing plasma cholesterol levels.
  • the proportion of non-esterified phytosterols used in the edible fat-based composition for a prepared food is between 3% and 15% by weight of the composition, and more preferably between 5 and 10% of the composition (or other percentage as described for food products herein).
  • a serving of food containing 10 grams of a fat-based composition would contain between 0.5g and 1.0 g of non-esterified phytosterols. This amount is consistent with current recommendations published by the U.S. Food and Drug Administration.
  • the edible fat-based composition is heated to a temperature of greater than 60°C, and preferably between 75°C and 150°C, or higher, to dissolve the non-esterified phytosterols in the composition.
  • a temperature of 60°C or below the rate of dissolution is slower than desirable, and the concentration of dissolved phytosterols in a fat-based medium is lower than generally desired to be commercially useful or practical.
  • the TRPs are formed by heating at least the edible fat-based composition to a temperature exceeding 60°C for a period of time sufficient to dissolve the non-esterified phytosterols in the fat, and subsequently cooling the composition (or the food containing this composition) to room temperature to cause the TRPs to be formed.
  • the invention features a method for reducing plasma cholesterol levels in mammals, including providing and regularly ingesting a heat- processed prepared food containing an edible fat-based composition that contains between 75% and 97% by weight of at least one triglyceride-based edible fat, and at least 3% by weight of non-esterified triglyceride-recrystallized phytosterols.
  • the phytosterols are soluble in the fat at a level of approximately 1.5% and the remainder (e.g., 1.5% from a total of 3%) is insoluble at room temperature.
  • the fat- based composition is substantially free of exogenous phytosterol-solubilizing and dispersing agents.
  • the insoluble phytosterols are heat-solubilized and subsequently cooled to form triglyceride-recrystallized phytosterols, i.e., TRPs.
  • TRPs triglyceride-recrystallized phytosterols
  • the TRPs when ingested are essentially as effective as fat-soluble esterified phytosterols in reducing plasma cholesterol levels.
  • the fat composition contains at least 5%, 7%, 10%, 12%, 15%), 17% or 20% by weight of non-esterified phytosterols (typically the phytosterols are soluble to a level of approximately 1.5% at room temperature and the remainder is insoluble).
  • non-esterified phytosterols typically the phytosterols are soluble to a level of approximately 1.5% at room temperature and the remainder is insoluble.
  • a method for preparing a TRP-containing fat- based composition includes (i) providing a triglyceride-based edible fat- containing composition that includes between 2% > and 25% by weight of non-esterified phytosterols and not more than 98% by weight of edible fat or oil, in which the composition is substantially free of exogenous phytosterol-solubilizing and dispersing agents, (ii) heating the composition to dissolve (preferably fully dissolve) the non- esterified phytosterols, and, (iii) cooling the composition to room temperature, allowing formation of TRPs.
  • the phytosterols are soluble in the edible fat or oil at room temperature to a level of approximately 1.5%, while the remainder is insoluble at room temperature.
  • the fat-containing composition is heated to a temperature of 60-180°C, usually 75-150°C.
  • a method for preparing a non-esterified phytosterol-fortified prepared food includes: (i) providing an edible fat- based composition that includes between 2% and 25% by weight of non-esterified phytosterols and between 75% and 98% by weight of at least one edible fat or oil, in which the composition is substantially free of exogenous phytosterol-solubilizing and dispersing agents, and one or more other ingredients for the prepared food if any such additional ingredients are used; (ii) cooking or otherwise heating the prepared food ingredients with the composition to allow the non-esterified phytosterols to dissolve in the oil or fat and enter or become integrated into the food product; and (iii) cooling the food product to room temperature to allow formation of TRPs in the composition within the prepared food.
  • the fat-based composition can be used as an ingredient mixed with other ingredients in the preparation of the prepared food, and/or the prepared food product can be cooked in the fat-based composition.
  • the phytosterols can be combined with the oil or fat in preparation of the prepared food.
  • the fat or oil and the phytosterols can be added as separate ingredients in such manner that the phytosterols will dissolve in the fat or oil upon heating of the combined ingredients.
  • only a portion of the phytosterols added as ingredients will become solubilized, e.g., where only a portion of the phytosterols are in contact with the fat or oil during heating.
  • the fat- based composition, or the oil or fat and the phytosterols are added as ingredients in preparing the prepared food, typically a number of different ingredients are blended or mixed such that the various ingredients are relatively uniformly distributed throughout the mixture.
  • the term "prepared" in the context of a "prepared food product” refers to a commercially processed and packaged food product containing multiple combined ingredients, in which the processing includes at least one step in which the assembled food product (or one or more triglyceride-based fat or oil ingredients that are either contacting, or being combined into the food product), are heated together with a suitable quantity of phytosterol ingredient(s), to a temperature sufficient to dissolve the phytosterols in the fat or oil, and often substantially higher than this temperature, and for a period of time sufficient to process, cook, fry or otherwise complete the heat- preparation of the food product. Upon cooling, a portion of the phytosterols recrystallize in a fat or oil component of the processed prepared food product.
  • Examples of such prepared food products include potato chips (containing at least potatoes, frying fat or oil, and phytosterols), French fries, corn chips, tortilla chips, popcorn, crackers, peanut butter, soybean butter, sesame seed butter and other nut kernel butters, mayonnaise, processed cheese, chocolate and the like.
  • potato chips containing at least potatoes, frying fat or oil, and phytosterols
  • French fries corn chips
  • tortilla chips popcorn
  • crackers peanut butter, soybean butter, sesame seed butter and other nut kernel butters
  • mayonnaise processed cheese, chocolate and the like.
  • fat may be used broadly and generally, referring to an edible triglyceride that may be either liquid (also specifically termed oil) or solid at room temperature (also specifically termed fat), and that is derived from a single vegetable source (e.g., soybean, cottonseed, corn) or an animal source (beef tallow, pork lard) or a blended combination of sources. Unless specifically limited to edible triglyceride compositions that are solid at room temperature, use of the term “fat” includes oils. Also unless clearly indicated to the contrary, the term “fat” also includes chemically and enzymatically modified triglyceride-based liquid and solid fats and blends thereof
  • the phrase "improved resistance to oxidation" for a fat that contains non- esterified phytosterols refers to a fat exhibiting at least a 10% reduced rate of degradation by oxidation in air, compared to oxidation of the same fat without phytosterols. This differential oxidation rate is particularly evident during heating of the oil, e.g., frying with the oil at a temperature of 160-190°C.
  • Oxidation rate is evidenced by one or more physical measurements such as dielectric constant measurement of polar oxidation products formed in the fat, AOM (accelerated oxidation measurement, OSI (oxidative stability index), or organoleptic quality (tasting f or rancidity).
  • AOM accelerated oxidation measurement
  • OSI oxidative stability index
  • organoleptic quality tacsting f or rancidity.
  • the extent of oxidative protection provided by non-esterified phytosterols dissolved in fat heated to 180°C is a function of the type of fat and the concentration of phytosterols in the fat. Improved resistance to oxidation is particularly evident in a vegetable oil containing polyunsaturated fatty acids, e.g., soybean, corn and canola oil.
  • the rate of oxidation i.e., formation of polar oxidation products
  • the rate of oxidation is at least 10% lower than the rate in the same oil lacking phytosterols.
  • the rate of oxidation is at least 20% lower, and more preferably, the rate is 30%, 40% or even 50% lower than the rate in the same oil lacking phytosterols.
  • partially oxidized refers to a fat-based composition that has been exposed to air either with or without heating, e.g., frying or baking and that has at least begun to accumulate oxidative by-products whose concentrations are measurable either in the oil or in the vapor above the oil by conventional means, e.g., by conductivity, dielectric constant, and free fatty acid content.
  • phytosterols are not recognized as antioxidants or as scavengers or quenchers of free-radicals or peroxides and hydroperoxides formed during oxidation of polyunsaturated fatty acid moieties.
  • Applicants have looked to literature describing various properties of cholesterol.
  • cholesterol fortification of a food product would be nutritionally undesirable and, indeed, phytosterol fortification is intended to reduce cholesterol uptake.
  • the cholesterol molecule is structurally related to the phytosterols, i.e., addition of an ethyl side group to beta- sitosterol generates cholesterol.
  • U.S. Pat. No. 6,214,534 by Horowitz et al. describes several UV light photodynamic quenchers including vitamins, thiols, cholesterol, and several other compounds that react with, and inactivate both free radicals and reactive forms of oxygen. Since free radicals, peroxides and hydroperoxides are produced during the oxidation of polyunsaturated fatty acid groups in triglycerides, phytosterols dissolved in fat may inactivate these reactive compounds, as with cholesterol described in the photodynamic system of Horowitz et al. While the phytosterols may act in this manner, the present invention is not limited by this explanation.
  • composition in the context of an oil or fat-based composition means that the composition is suitable for use in mammalian, e.g., human, foods, dietary supplements and pharmaceutical preparations.
  • exogenous phytosterol-solubilizing and dispersing agents refers to agents other than triglycerides in the prior art, that have been added to triglyceride- based oils and fats to promote the cholesterol-lowering efficacy of phytosterols (see discussion above in the Background section).
  • a partial list of these agents includes monoglycerides, diglycerides, lecithin, vitamin E, the sorbitans and other surfactants, and fatty acids chemically esterified with phytosterols.
  • substantially free referring to any presence of exogenous solubilizing and dispersing agents for phytosterols, means that either zero percent, or in any event, less than 50% (and preferably less than 25%>) of the amount of such an agent or agents that would be required in the absence of triglycerides, to achieve solubilization or dispersal of non-esterified phytosterols (at room temperature) that have been added to the referenced composition.
  • the phytosterols are recrystalhzed in triglycerides, triglycerides alone are sufficient for phytosterol bioavailability, i.e.., effectiveness in plasma cholesterol reduction. Therefore, any addition of such a non-triglyceride solubilizing or dispersing agent to a fat-based composition containing TRPs is considered gratuitous and optional.
  • phytosterol refers to any of a group of sterols derived from plants (see examples below in Example 1).
  • non-esterified phytosterols refers to forms of phytosterols that are free of ester chemical side chains.
  • esterified phytosterols are most commonly fatty acid-esterified phytosterols manufactured to promote phytosterol solubility in fat.
  • Non-esterified phytosterols are defined herein to include both the non- esterified sterol and stanol forms of phytosterols (see Example 1 below).
  • phytosterols are dissolved in oil or fat before recrystallization, and therefore the particle size, texture, etc. of the material can be coarse for reasons of economy, i.e., chemical dissolution reduces the material to molecular dimensions. Dissolution of more costly forms of phytosterols, e.g., ultrafine micron-sized phytosterol powders, would be economically wasteful, but can also be done.
  • the composition which includes between 75% and 98% by weight of at least one triglyceride-based edible oil or fat, allows between 2% and 25% by weight of non- esterified phytosterols to be added to the same composition.
  • a 3% to 10% by weight concentration range is a preferred range. Accordingly, at the 3% level, a food that contains lOg of fat per serving will provide at least 0.3g of phytosterols per serving.
  • the composition may include as little as 50% by weight of at least one triglyceride-based edible oil or fat, to allow between 3% and 50% by weight of non-esterified phytosterols to be added to the same composition.
  • the process of treating the non-esterified phytosterols by "heating, fully dissolving, and cooling” refers to a process that: (i) heats the phytosterols together with triglyceride-based fat or oil (and optionally other food ingredients constituting a prepared food product) to a temperature of greater than 60°C until the phytosterols have dissolved, and then (ii) cooling the heated product and allowing the triglycerides to associate with the recrystallizing phytosterols. Flash-chilling with chilled air or with a chilled water jacket may tend to precipitate and segregate the phytosterols from the triglycerides, preventing optimal recrystallization.
  • TRPs triglyceride-recrystallized phytosterols
  • recrystalhzed is distinguished from the term “solubilized”( in which the phytosterols are dissolved to form a clear solution). Recrystalhzed is meant to indicate that the phytosterols after initially being dissolved in one or more triglyceride-based fats or oils, are allowed to cool and recrystallize in the oil or fat.
  • Applicants have determined that such recrystallization results in fats and/or oils, i.e., triglycerides, becoming intimately associated with crystallizing phytosterols.
  • the resulting products are mixed and/or interrupted crystal structures having melting temperatures reduced below that of the phytosterols alone.
  • these physically destabilized, triglyceride-containing crystals are more easily emulsified and/or dissolved in the mammalian gut, resulting in improved phytosterol bioavailability and therefore more effective plasma cholesterol reduction in vivo.
  • a proportion of the phytosterols is soluble in the fat at room temperature (typically at a concentration of about 1.5%). Therefore, when a combination of phytosterols and fat is heated to dissolve solidified (crystallized) phystosterols and then cooled, phytosterols that cannot remain in solution at room temperature solidify or recrystallize, but a portion remains dissolved in the fat.
  • triglyceride-recrystallized phytosterols or “TRPs” includes both the dissolved phytosterols as well as the resolidified or recrystalhzed phytosterols.
  • the term "effective" refers to the extent to which plasma cholesterol levels in mammals are reduced by regular, e.g., daily, twice daily, or thrice daily ingestion of the recommended 1-2 gram dose (or the appropriate divided dose) of phytosterols. In a random population of human adults, a 5% to 15% or greater lowering of total cholesterol in the plasma caused by ingestion of phytosterols is considered effective.
  • esterified phytosterols refers to phytosterols (plant sterols and stanols) that have been joined through an ester linkage to fatty acids using a chemical, enzymatic, combination, or other process.
  • reduced surface oiliness means that upon routine handling of the prepared food, less oil is transferred from the food to ones hands (or to an absorbant surface) than would otherwise occur if the food were prepared with the oil or fat alone (see Example 5 below).
  • microcrystalline phytosterol product can be mixed with a sweetening agent and water or alternatively, mixed with another carrier such as fat to form a microparticulate emulsion.
  • a sweetening agent and water or alternatively, mixed with another carrier such as fat to form a microparticulate emulsion.
  • another carrier such as fat
  • phytosterols are recrystalhzed with triglycerides (e.g., vegetable oil, shortening, or the like).
  • the first step involves heating the triglyceride(s) and phytosterol(s) until the phytosterols are dissolved.
  • This phytosterol-triglyceride solution is used to contact, or be combined with the food product being fried, cooked or otherwise heated. (Alternatively, the fats and the phytosterols are added as separate ingredients in the preparation of a prepared food.)
  • the prepared food product is cooled (preferably by contacting the heated food product with ambient air).
  • phytosterols that have been recrystalhzed in vegetable oil, e.g., soybean oil, tend to form a diversity of macrocrystalline structures spanning tens or hundreds of microns.
  • This material when tasted, has a surprisingly soft and agreeable mouth feel, and includes elongated hexagonal crystals, radially extending branched crystalline needle structures (appearing as wispy ball-shaped structures), and large extended flat plate crystals.
  • phytosterols that are recrystalhzed by quick-chilling to room temperature tend to form harder, smaller, more homogeneous needle-like micro-crystals having diameters of only a few microns, i.e., 1-4 microns.
  • the temperature required to re-dissolve the above crystals in the surrounding vegetable oil differs significantly depending upon the rapidity of recrystallization. For example, 10% by weight soybean-derived phytosterols that were recrystalhzed at room temperature in soybean oil, redissolved in the oil at a temperature of 65°C. On the other hand, the more rapidly ice-recrystallized phytosterols described above required a higher temperature (72°C) to be redissolved. By comparison, the same amount of phytosterol (as a dry powder) initially placed in soybean oil, required a temperature of nearly 85°C to be dissolved.
  • Non-esterified phytosterols are known to have a very limited solubility (to a concentration of approximately 1.5% by weight) in an edible oil or fat at room temperature. Nevertheless, between 2% and 25% by weight of non-esterified phytosterols (e.g., semi-pure or purified phytosterols from soybeans or pine tree tall oils), can be readily and conveniently dissolved in edible oil or fat by heating to a temperature of 60°C or greater, and preferably 75°C -100°C or above (the required temperature depending upon the concentration of phytosterols to be dissolved).
  • non-esterified phytosterols e.g., semi-pure or purified phytosterols from soybeans or pine tree tall oils
  • TRP Triglyceride-Recrystallized Phytosterol composition or complex
  • the TRP composition formed in this manner has been found to be as potent in the mammalian diet at reducing the levels of plasma and liver cholesterol as fatty acid-esterified phytosterols that are fully soluble at room temperature.
  • non-esterified phytosterols In the first direct comparison between non-esterified phytosterols and equivalent amounts of phytosterols as sterol esters in the same experiment, it was found that non-esterified phytosterols fully dissolved in oil by heating (>60 degrees C, and preferably >80 degrees C), and provided equivalent (or even greater) reductions in plasma and liver cholesterol as compared to equivalent amounts of esterified sterols.
  • the term "greater” means that the cholesterol reductions measured and reported herein and in the Hayes reference are greater than those reported by Ntanios and Jones (Biochim. Biophys. Ada (1998) 1390:237-244) for the same levels of sterols, in which the sterols were incompletely dissolved in fat. While TRPs may have been accidentally produced in the past in the course of heating and cooling non-esterified phytosterols and fats, their utility for plasma cholesterol reduction would not have been recognized due to their poor room temperture solubility.
  • the presently described TRP composition is more convenient and cost- effective than esterified phytosterols or phytosterol-containing compositions that have been supplemented with solubilizers, emulsifiers, antioxidants and other additives for inclusion in foods.
  • the TRP composition also has a significant advantage over the finely milled and microcrystalline powdered forms of phytosterols described by Tiainen et al. and Jones et al., in light of the considerable cost associated with producing these micron-sized powders.
  • the present composition is particularly useful in preparing fat- based foods such as shortening, margarine, mayonnaise, salad dressing, peanut butter and the like, and processed food products including fried and baked snack foods.
  • TRP-containing composition is reduced. While other investigators have found that finely milled or microcrystalline preparations of non-esterified phytosterols that have not been initially heat-solubilized in an oil or fat, can also function efficiently to reduce mammalian plasma cholesterol levels, the additional benefits described above are obtained only after heat-solubilization. For example, heat-solubilization in a triglyceride-based edible oil allows non-esterified phytosterols to freely enter a food product as it is being fried in the oil, whereas particles of phytosterols would be excluded. Likewise, suspended particles would not be expected to improve the oxidative stability of an oil.
  • the fat or oil used as a vehicle or carrier for the phytosterol herein is a conventional triglyceride-based cooking fat or oil that is substantially free of phytosterol solubilizing agents, dispersants and/or detergents (collectively termed "oil emulsifiers or additives").
  • oil emulsifiers or additives include natural vegetable oils, interesterified fats and oils, and partially hydrogenated vegetable oils, animal fats and combinations thereof.
  • the presently described triglyceride- based composition contains substantial amounts of insoluble phytosterol (recrystalhzed in fat) rather than solubilized phytosterol, and is substantially free of the above- described oil additives for dispersing or solubilizing phytosterols.
  • the composition is particularly useful in preparing fat-containing foods that do not require oil transparency at ambient temperatures. This is true of margarines, shortenings, mayonnaise, cheese and other dairy fat-containing products, some salad dressings, and many other foods including processed foods that are fried, baked or otherwise prepared by cooking or heating in, or in combination with fat or oil. Examples of such foods include the snack food category, e.g., potato chips, crackers, and the bakery category, e.g., donuts, pies, cakes, and the like.
  • the present invention describes compositions and methods for introducing substantially fat-insoluble non-esterified phytosterols into foods, including snack foods, by means of the standard fat or oil that is used in the frying or baking of such foods. It was the inventors' intention to compare the efficacy of using non-esterified phytosterol preparations recrystalhzed in edible fat and used in foods, e.g., fried foods, with that of more costly diglyceride-solubilized or fatty acid esterified phytosterols in limiting cholesterol absorption in the gut, and lowering plasma cholesterol levels.
  • the phytosterols recrystalhzed in fat that has been incorporated into such foods are very effective, i.e., bioavailable, in reducing plasma and liver cholesterol levels. It is believed that this cholesterol-lowering efficacy compares favorably with that of fully solubilized phytosterol preparations (e.g., phytosterols esterified with fatty acids to assure solubility in fat-containing products such as Benecol® and Take Control® margarines).
  • fully solubilized phytosterol preparations e.g., phytosterols esterified with fatty acids to assure solubility in fat-containing products such as Benecol® and Take Control® margarines.
  • the presence of 5-10% or more by weight of phytosterol that has been recrystalhzed with triglycerides in the oil portion of fried snack food has been found to decrease the surface oiliness of fried food when compared to food fried in oil lacking the phytosterol.
  • Applicants have also found that the presence of either soybean oil-derived phytosterols or tall oil-derived phytosterols in vegetable oil during frying, helps in chemically stabilizing the oil against oxidation by reducing the rate of appearance and the amount of polar breakdown products in the oil.
  • the phytosterols replace a portion of the oil in such a blend
  • the phytosterols also serve to reduce the caloric fat content of a food cooked in the blend.
  • the present invention also provides methods for decreasing the surface oiliness of fried foods, and the resulting fried foods, and methods for providing reduced calorie food, utilizing TRPs as described herein.
  • bioavailability for a given quantity of phytosterol means the potency of that particular physical and/or chemical form of phytosterol in lowering the plasma level of total and LDL cholesterol.
  • non-esterified phytosterols e.g., soybean oil-derived mixed prilled sterols or stanols or tall oil-derived sterols and stanols
  • concentrations of between 2% and 25% by weight non- esterified phytosterols can be conveniently and rapidly dissolved by mixing or other agitation in diverse oils, fats and fat-containing foods, e.g., cooking or salad oil, shortening, peanut butter and dairy cream, heated to a temperature of greater than 60°C, and preferably between 75°C and 150°C, or above.
  • a heated oil or fat e.g., corn, canola, cottonseed, soybean oil, or palm oil that contains heat-solubilized phytosterols is useful in the preparation (e.g. , frying and baking) of potato chips and other snack foods.
  • heat-solubilized phytosterols are cooled and recrystalhzed in such fats or fat-containing foods, their ability to lower plasma cholesterol levels is excellent (see nutritional studies below).
  • the fat compositions and food products of the present invention can be prepared by conventional methods, with the addition of phytosterols (e.g., as described herein). Persons familiar with preparation of fat compositions and food products can routinely select suitable components for a particular product.
  • each cholesterol-lowering regimen i.e., sterols and stanols, each tested separately after heating with dietary fat; or stanols combined with either 3% or 6% by weight of the above emulsifier in the heated dietary fat
  • sterols and stanols each tested separately after heating with dietary fat; or stanols combined with either 3% or 6% by weight of the above emulsifier in the heated dietary fat
  • TC total cholesterol value
  • soybean oil-derived prilled phytosterols containing up to 4% by weight brassicasterol, 30% campasterol, 20% stigmasterol, and 40% beta-sitosterol.
  • each phytosterol in cooking oil was measured by fully dissolving a graded series of concentrations (from 1% to 5% by weight, in steps of 0.5%) of each sample in soybean oil heated to 150°C, then cooling the samples to room temperature and waiting 24 hours for any supersaturating phytosterol to crystallize. All phytosterols appeared soluble in room temperature cooking oil at a concentration of 1.5% by weight, while all showed precipitates at concentrations of 2.0% and higher.
  • phytosterols can be conveniently dissolved in fat when heated only to 60°C . Temperatures greater than 60°C are suggested for fully dissolving these higher concentrations of phytosterols in fats and oils, and preferably temperatures of 75°C, 100°C or even greater to speed the solubilization process prior to allowing recrystallization to occur.
  • temperatures as low as 50°C-60°C may eventually promote phytosterol solubilization, albeit at a much slower rate than solubilization at 75°C-100°C, prior to cooling and formation of TRPs.
  • Example 2 Crystalline Phytosterol Composition Formed With Triglycerides.
  • One part by weight tall oil-derived phytosterol or one part by weight soybean- derived prilled phytosterol powder (non-esterified phytosterols) described above were each heated with nine parts soybean oil. The temperature required to solubilize these 10%) by weight powders in oil was approximately 75-85°C. From Example 1 it was estimated that approximately 8.5% by weight phytosterols (out of 10% total) recrystalhzed in the oil following cooling to room temperature. Phase contrast microscopic examination (600x magnification) of the solids showed a mixture of extended needle and plate-type crystalline material suspended throughout the mixture, that differed markedly from the amorphous solids originally placed in the triglyceride oil.
  • Applicants wished to determine whether admixing and dissolving a substantial concentration of phytosterol (e.g., 10% by weight) in a heated cooking oil, would alter the chemical properties or physical cooking properties of the cooking oil. For example, would the presence of phytosterol accelerate the rate of oxidation or rancidity development in the oil, would the oil retain its original flavor, and would the cooking time for a particular food at a specified temperature be appreciably altered? Additionally it was of interest to compare the extent of oil uptake by a food fried in vegetable oil with and without the phytosterol.
  • phytosterol e.g. 10% by weight
  • soybean oil-derived phytosterols were dissolved in a one pound quantity of heated canola oil, and approximately 20 successive small batches of potato chips (russet potatoes, approximately 20 slices, 3-4g per slice ) were fried in each of these oils at 170°C
  • phytosterols sterols, stanols or mixtures thereof
  • added to edible oils and fats used in prepared food products will also provide increased shelf-stability for these products, via resistance to oil oxidation and rancidity development at room temperature.
  • Phytosterol analysis employed the following method: Oil plus phytosterol contained in potato chips was first extracted into chloroform. A portion of the chloroform (100 ⁇ l) was evaporated, redissolved in a small quantity of isopropyl alcohol (20 ⁇ l), and then assayed using Test Kit #352 for cholesterol and other sterols (Sigma Chemical Company, St. Louis, MO). A test standard was prepared containing
  • Example 5 Surface Oiliness of Food Fried in Phytosterol-Containing Vegetable Oil.
  • phytosterols e.g., 3% by weight or more of phytosterols
  • soybeans or tall oils
  • their crystallization causes the oil to solidify.
  • the degree of firmness of the solid depends upon the phytosterol content of the oil.
  • PHVO partially hydrogenated vegetable oil
  • a method was devised to measure the relative surface oiliness of potato chips.
  • Potato chips fried for 1 minute at 180°C in either canola oil or canola plus 10% by weight soybean oil-derived phytosterols were cooled for at least one hour.
  • An assay of the total fat content of these two groups of chips (method, see Example 4) showed that the former contained 26% by weight canola oil while the latter contained 29% by weight canola oil plus phytosterols.
  • Single potato chips were selected (weighing approximately 1.2g each) and were gently but thoroughly wiped three times on both sides with a single pre-weighed paper tissue (Kimwipe®, Kimberly Clark Paper
  • Example 6 Recrystalhzed Non-Esterified Phytosterols in Dietary Fat Provide Significant Reduction in Plasma Cholesterol Levels.
  • the aim of this study was to determine the hypocholesterolemic efficacy of free, i.e., non-esterified phytosterols (from soybean oil) in a cholesterol-responsive animal model.
  • Non-esterified sterols were allowed to freely crystallize in the fat component of the mixture as it cooled. All gerbils were given free access to water, and food was provided daily in the predetermined amounts to meet their caloric requirement for growth and maintenance. Animals were housed in groups of 2-3 and were kept in a controlled environment with a 12 h light-dark cycle (light on 18:00 h).
  • HDL- C was assayed in the supernatant after sodium phosphotungstate-Mg2+ precipitation of lipoproteins containing apolipoprotein B and E (Boehringer Mannheim Diagnostics, procedure 543004) according to the procedure described by Weingard and Daggy (Clin. Chem. 1990, 36: 575).
  • Plasma triglycerides were not statistically reduced by sterol supplementation.
  • Example 7 Non-Esterified Sterols Absorbed by Potato Chips During Frying or Dissolved and Recrystalhzed in Free Dietary Fat Can Reduce Plasma Cholesterol Levels.
  • the aim of this study was to evaluate the hypocholesterolemic efficacy of potato chips enriched with non-esterified sterols (derived from soybean oil) using the same animal model system (see Example 6).
  • Phytosterol-enriched potato chips Potato chips were fried in canola oil that was either supplemented or not supplemented with soybean oil-derived phytosterols (10%) by weight). When phytosterols were added, they rapidly dissolved in the oil that had been heated to 180°C prior to frying the chips.
  • control diet (see Table 4 for dietary composition) provided no sterols but contained regular commercial potato chips fried in canola oil, to provide the same level of carbohydrate and the standard level of dietary fat (13.7%). All other experimental conditions, including animal maintenance, feeding, sample collecting and analytical methods were the same as described above (see Example 6).
  • TRP triglyceride-recrystallized phytosterol
  • Vegetable Oil Triglycerides Can Prevent Oil Separation in Peanut Butter.
  • This partial solidification prevents the natural oil separation process that is regarded as an undesirable annoyance in natural peanut butter.
  • This percentage of phytosterol provides 0.9 grams sterol per 32g serving of peanut butter or approximately 100% of the daily amount of plant sterols recommended for achieving a 10-15% reduction in the human plasma cholesterol level.
  • This daily dose is approximately equivalent to the recommended dose of 1.3-1.5 grams of sterol esters (as provided in commercial cholesterol-reducing margarines) in which only 60% by weight of the sterol esters consists of the active sterol moiety.
  • Example 9 Non-Esterified Phytosterols Dissolved and Subsequently Recrystalhzed in Cocoa Butter Triglycerides Can Be Incorporated into Chocolate.
  • Cocoa Butter has a melting temperature above room temperature but below body temperature (37°C). This property allows chocolate, a processed food containing approximately 30% by weight cocoa butter, to remain solid at room temperature, and to melt in ones mouth. Soybean oil phytosterols were added to cocoa butter at a concentration of 10% by weight, and were dissolved by heating. The cocoa butter was subsequently cooled and solidified.
  • Oxidation of oils was determined using "Foodoiis Sensor” which measures the dielectric constant of polar compounds formed in the oil during heating. Values indicates relative (to baseline) increases in peroxides, acids and other polar components formed in the oil during heating.
  • the oils (5g) were heated with or without prilled phytosterols in 100mL beakers at 170° C.

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Abstract

L'invention concerne un produit alimentaire préparé pour l'ingestion chez les mammifères ainsi que des procédés pour préparer lesdits produits. Ledit produit alimentaire comprend une composition résistante à l'oxydation, à base de graisses sensiblement sans agents exogènes de solubilisation et de dispersion pour les phytostérols. Ladite composition à base de graisses comprend entre 75 et 98 % en poids d'au moins une graisse ou huile alimentaire à base de triglycéride, et entre 2 et 25 % en poids de phytostérols non estérifiés. Généralement, environ 1, 5 % en poids des phytostérols restent solubles à la température ambiante, et entre 0,5 et 23, 5 % en poids sont transformés en phytostérols recristallisés par triglycérides (TRP). Ladite composition à base de graisse qui peut être partiellement oxydée dans la nourriture préparée par exposition à l'air (et de manière générale à la chaleur), contient une quantité réduite de sous-produits oxydants par rapport à une composition à base de graisse similaire ne contenant pas lesdits phytostérols non estérifiés.
PCT/US2002/036809 2001-11-16 2002-11-14 Produits alimentaires prepares contenant des phytosterols non esterifies recristallises par triglycerides WO2003043433A1 (fr)

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AT02789698T ATE446013T1 (de) 2001-11-16 2002-11-14 Fertignahrung, die aus triglyceriden umkristallisierte nichtveresterte phytosterole enthalten
DE60234120T DE60234120D1 (de) 2001-11-16 2002-11-14 Fertignahrung, die aus triglyceriden umkristallisierte nichtveresterte phytosterole enthalten
AU2002352747A AU2002352747A1 (en) 2001-11-16 2002-11-14 Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
EP02789698A EP1453386B9 (fr) 2001-11-16 2002-11-14 Produits alimentaires prepares contenant des phytosterols non esterifies recristallises par triglycerides
US10/677,634 US7144595B2 (en) 2001-11-16 2003-10-01 Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
US11/475,575 US7709038B2 (en) 2001-11-16 2006-06-26 Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
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WO2007067884A1 (fr) * 2005-12-05 2007-06-14 Bunge Oils, Inc. Aliments frits contenant des phytosterols et procedes permettant d'ameliorer les caracteristiques liees a l'amelioration de la sante
US7575768B2 (en) 2005-09-07 2009-08-18 Brandeis University Dietary supplements and prepared foods containing triglyceride-recrystallized non-esterified phytosterols
US7709038B2 (en) 2001-11-16 2010-05-04 Brandeis University Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
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US11806352B2 (en) 2010-05-19 2023-11-07 Upfield Europe B.V. Theobromine for increasing HDL-cholesterol
WO2012038226A1 (fr) 2010-09-22 2012-03-29 Unilever Nv Pâtes à tartiner continues de matière grasse alimentaire
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DE60234120D1 (de) 2009-12-03
ATE446013T1 (de) 2009-11-15
EP1453386B1 (fr) 2009-10-21
EP1453386A4 (fr) 2005-12-21
EP1453386A1 (fr) 2004-09-08
US20030096035A1 (en) 2003-05-22

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